2-(2-methylbenzylamino)acetaldehyde dimethyl acetal | 54879-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-methylbenzylamino)acetaldehyde dimethyl acetal
• 英文别名: 2,2-dimethoxy-N-[(2-methylphenyl)methyl]ethanamine
• CAS: 54879-85-5
• 化学式: C₁₂H₁₉NO₂
• mdl: MFCD00963820
• 分子量: 209.288
• InChiKey: LLDXYIFPROPAFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-methylbenzylamino)acetaldehyde dimethyl acetal 在 四氯化钛 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 1,2,3,4-tetrahydro-8-methyl-2-tosylisoquinoline
  参考文献：
  名称：

  通过TiCl4介导的环化和Et3SiH还原合成四氢异喹啉

  摘要：

  摘要报道了一种通用且有效的伸缩反应序列，用于合成四氢异喹啉（THIQs），该序列使用TiCl4促进苄氨基缩醛衍生物的环化反应，并使用Et3SiH还原中间体4-羟基-THIQ。此方法是对经典Pomeranz-Fritsch和相关反应的补充，因为它可以耐受吸电子取代基并允许使用8位取代的THIQ。

  DOI：

  10.1016/j.cclet.2019.09.023
• 作为产物：
  描述：

  2,2-二甲氧基-N-(2-甲基亚苄基)乙胺 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 2-(2-methylbenzylamino)acetaldehyde dimethyl acetal
  参考文献：
  名称：

  Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 2. Structure-activity relationships at the phenethylamine binding site

  摘要：

  1-Aralkylimidazole-2-thiones have been shown to be potent multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1). In the present study, a series of 1-benzylimidazole-2-thiones was prepared to explore the effects of substitution in the benzyl ring on the inhibition of DBH. A detailed structure-activity relationship for in vitro activity was discovered and this was shown by a modified Hansch analysis to correlate (r = 0.91) with four key structural features of the benzyl ring: the presence of a hydroxyl at the 4-position, molar refractivity at the 3-, 4-, and 5-positions, inductive effects of the substituents at the 3-, 4-, and 5-positions, and pi-electron density. The affinity (Kis) of eight substituted inhibitors for DBH was shown to correlate (r = 0.75) with the affinity (KD) of comparably substituted tyramines for the ternary DBH-oxygen-tyramine complex. This correlate is used to support the hypothesis that binding of inhibitor to DBH occurs in a fashion that mimics the binding of tyramine substrates. The most potent inhibitors were selected for study in vivo in the spontaneously hypertensive rat model of hypertension. The changes in vascular dopamine and norepinephrine levels that resulted from oral administration of the inhibitors corresponded to the observed reduction in mean arterial blood pressure. A divergence between in vitro potency and in vivo efficacy upon oral dosing was noted and is suggested to result from an in vivo metabolic conjugation of the phenolic group of inhibitor.

  DOI：

  10.1021/jm00386a008

文献信息

• [EN] MTP INHIBITING ARYL PIPERIDINES OR PIPERAZINES SUBSTITUTED WITH 5-MEMBERED HETEROCYCLES<br/>[FR] PIPERIDINES D'ARYLE OU PIPERAZINES SUBSTITUEES PAR DES HETEROCYCLES A 5 RAMIFICATIONS INHIBANT LA MTP
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005085226A1

  公开（公告）日：2005-09-15

  The present invention is concerned with novel aryl piperidine or piperazine compounds substituted with certain 5-membered heterocycles having apoB secretion/MTP inhibiting activity and concomitant lipid lowering activity. The invention further relates to methods for preparing such compounds, pharmaceutical compositions comprising said compounds as well as the use of said compounds as a medicine for the treatment of hyperlipidemia, obesity and type II diabetes (Formula (I)). The invention further relates to methods for preparing such compounds, pharmaceutical compositions comprising said compounds as well as the use of said compounds as a medicine for the treatment of atherosclerosis, pancreatitis, obesity, hyper­triglyceridemia, hypercholesterolemia, hyperlipidemia, diabetes and type II diabetes.

  本发明涉及新颖的芳基哌啶或哌嗪化合物，其被某些含有apoB分泌/MTP抑制活性和伴随的降脂活性的5-成员杂环取代。该发明还涉及制备这种化合物的方法，包括所述化合物的药物组合物以及将所述化合物用作治疗高脂血症、肥胖症和2型糖尿病的药物的用途（公式（I））。该发明还涉及制备这种化合物的方法，包括所述化合物的药物组合物以及将所述化合物用作治疗动脉粥样硬化、胰腺炎、肥胖症、高甘油三酯血症、高胆固醇血症、高脂血症、糖尿病和2型糖尿病的药物的用途。
• [EN] CYCLIC AMINE DERIVATIVES HAVING BETA2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY<br/>[FR] DÉRIVÉS D'AMINE CYCLIQUE AYANT UNE ACTIVITÉ AGONISTE DE RÉCEPTEUR ADRÉNERGIQUE BÊTA-2 ET ANTAGONISTE DE RÉCEPTEUR MUSCARINIQUE
  申请人：ASTRAZENECA AB

  公开号：WO2011048409A1

  公开（公告）日：2011-04-28

  Compounds of formula (I) having activities at muscarinic and β2-receptors (MABAs) for use in therapy.

  具有在毒蕈碱受体和β2受体（MABAs）上活性的化合物（I）的公式，用于治疗。
• Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands
  作者：Aniruddha Biswas、Subarna Pan、Rajarshi Samanta

  DOI：10.1021/acs.orglett.2c00127

  日期：2022.3.4

  was developed for the synthesis of heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. The developed method offered QUINOX and related congeners in a simple manner. A wide scope of important heterobiaryls was achieved with high site selectivity. The synthesized naphthols were transformed into the privileged related P,N ligands. Suitable resolution methods

  开发了一种有效且直接的方法，用于在廉价的 Cu(II) 催化下使用容易获得的N-氧化物和重氮萘醌合成杂二芳基化合物。所开发的方法以简单的方式提供了 QUINOX 和相关同类物。以高位点选择性实现了范围广泛的重要杂二芳基化合物。合成的萘酚被转化为特权相关的 P,N 配体。合适的拆分方法可以直接提供相应的轴向手性杂二芳基化合物。
• Ultrasound assisted one-pot synthesis of benzo-fused indole-4,9-dinones from 1,4-naphthoquinone and α-aminoacetals
  作者：Quang H. Luu、Jorge D. Guerra、Cecilio M. Castañeda、Manuel A. Martinez、Jong Saunders、Benjamin A. Garcia、Brenda V. Gonzales、Anushritha R. Aidunuthula、Shizue Mito

  DOI：10.1016/j.tetlet.2016.04.031

  日期：2016.5

  A one-pot synthesis of benzo[f]indole-4,9-diones from 1,4-naphthoquinone with alpha-aminoacetals has been developed. This method provides a straightforward synthesis of benzo[f]indole-4,9-diones via intramolecular nucleophilic attack of aminoquinones to aldehydes under mild reaction conditions. The detailed mechanism was also investigated. (C) 2016 Elsevier Ltd. All rights reserved.
• MTP INHIBITING ARYL PIPERIDINES OR PIPERAZINES SUBSTITUTED WITH 5-MEMBERED HETEROCYCLES
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1751131A1

  公开（公告）日：2007-02-14